Biosynthetic studies on the botcinolide skeleton: new hydroxylated lactones from Botrytis cinerea.

José L Reino, Rosa M Durán-Patrón, Mourad Daoubi, Isidro G Collado, Rosario Hernández-Galán

Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apdo 40, 11510 Puerto Real, Cádiz, Spain.

The Journal of organic chemistry 2006 Jan 20

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reaction: see text] The biosynthetic origin of the botcinolide skeleton was investigated by means of feeding 13C- and 2H-labeled precursors to Botrytis cinerea. Three new compounds, two homobotcinolide derivatives, 3-O-acetylhomobotcinolide (5) and 8-methylhomobotcinolide (6), and a new 11-membered lactone (7), were isolated. Their structures were elucidated on the basis of spectroscopic data, including one-bond and long-range 1H-13C correlations. The relative stereochemistries were determined by combined analyses of NOE data and 1H-1H coupling constants. According to the results of feeding experiments with 13C- and 2H-labeled acetate and l-S-methylmethionine, 5 is an acetate-derived polyketide whose methyl groups originate from l-S-methylmethionine. This is a rare example of the incorporation of a methyl from methionine into a supposed C3 starter unit of the polyketide synthesis.

Citation

José L Reino, Rosa M Durán-Patrón, Mourad Daoubi, Isidro G Collado, Rosario Hernández-Galán. Biosynthetic studies on the botcinolide skeleton: new hydroxylated lactones from Botrytis cinerea. The Journal of organic chemistry. 2006 Jan 20;71(2):562-5